Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
  • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
  • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
  • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Definitions

• the present invention relates to heterocyclic substituted isoxazolidines compounds, compositions containing these compounds and methods for controlling fungi by the use of a fungitoxic amount of these compounds.
• novel heterocyclic substituted isoxazolidine compounds of the present invention have the Formula (I)
• the aforementioned (C 1 -C 12 )alkyl, (C 2 -C 8 )alkenyl, (C 2 -C 8 )alkynyl and (C 3 -C 7 )cycloalkyl groups may be optionally substituted with up to three substituents selected from the group consisting of nitro, trihalomethyl and cyano.
• alkyl includes both branched and straight chained alkyl groups from 1 to 12 carbon atoms.
• Typical alkyl groups are methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, isobutyl, t-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, isooctyl, nonyl, decyl, undecyl, dodecyl and the like.
• haloalkyl refers to an alkyl group substituted with 1 to 3 halogens.
• alkenyl refers to an ethylenically unsaturated hydrocarbon group, straight or branched, having a chain length of 2 to 12 carbon atoms and 1 or 2 ethylenic bonds.
• haloalkenyl refers to an alkenyl group substituted with 1 to 3 halogen atoms.
• alkynyl refers to an unsaturated hydrocarbon group, straight or branched, having a chain length of 2 to 12 carbon atoms and 1 or 2 acetylenic bonds.
• cycloalkyl refers to a saturated ring system having 3 to 7 carbon atoms.
• aryl is understood to be phenyl or napthyl, which maybe further substituted with up to three substituents selected from the group consisting of halogen, cyano, nitro, trihalomethyl, phenyl, phenoxy, (C 1 -C 4 )alkyl, (C 1 -C 4 )alkylthio, (C 1 -C 4 )alkylsulfoxide (C 1 -C 6 )alkoxy and halo(C 1 -C 4 )alkyl.
• Typical aryl substituents include but are not limited to 4-chlorophenyl, 4-fluoro-phenyl, 4-bromophenyl, 2-methoxyphenyl, 2-methylphenyl, 3-methyphenyl, 4-methyl-phenyl, 2,4-dibromophenyl, 3,5-difluorophenyl, 2,4,6-trichlorophenyl, 4-methoxy-phenyl, 2-chloronapthyl, 2,4-dimethoxyphenyl, 4-(trifluoromethyl)phenyl and 2-iodo-4-methylphenyl.
• heterocyclic refers to a substituted or unsubstituted 5 or 6 membered unsaturated ring containing one, two or three heteroatoms, preferably one or two heteroatoms selected from oxygen, nitrogen and sulfur; or is a bicyclic unsaturated ring system containing up to 10 atoms including one heteratom selected from oxygen, nitrogen and sulfur.
• heterocycles include, but are not limited to, 2-, 3- or 4-pyridinyl, pyrazinyl, 2-, 4-, or 5-pyrimidinyl, pyridazinyl, triazolyl, imidazolyl, 2 - or 3-thienyl, 2- or 3-furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, quinolyl and isoquinolyl.
• the heterocyclic ring may be optionally substituted with up to two substituents independently selected from (C 1 -C 4 )alkyl, halogen, cyano, nitro and trihalomethyl.
• aralkyl is used to describe a group wherein the alkyl chain is from 1 to 10 carbon atoms and can be branched or straight chain, preferably a straight chain, with the aryl portion, as defined above, forming a terminal portion of the aralkyl moiety.
• Typical aralkyl moieties are optionally substituted benzyl, phenethyl, phenpropyl and phenbutyl moieties.
• Typical benzyl moieties are 2-chlorobenzyl, 3-chlorobenzyl, 4-chlorobenzyl, 2-fluorobenzyl, 3-fluorobenzyl, 4-fluorobenzyl, 4-trifluoromethylbenzyl, 2,4-dichlorobenzyl, 2,4-dibromobenzyl, 2-methylbenzyl, 3-methylbenzyl, and 4-methylbenzyl.
• Typical phenethyl moieties are 2-(2-chloro-phenyl)ethyl, 2-(3-chlorophenyl)ethyl, 2-(4-chlorophenyl)ethyl, 2-(2-fluorophenyl)-ethyl, 2-(3-fluorophenyl)ethyl, 2-(4-fluorophenyl)ethyl, 2-(2-methylphenyl)ethyl, 2-(3-methylphenyl)ethyl, 2-(4-methylphenyl)ethyl, 2-(4-trifluoromethylphenyl)ethyl, 2-(2-methoxyphenyl)ethyl, 2-(3-methoxyphenyl)ethyl, 2-(4-methoxyphenyl)ethyl, 2-(2,4-dichlorophenyl)ethyl, 2-(3,5-dimethoxyphenyl)ethyl.
• Typical phenpropyl moieties are 3-phenylpropyl, 3-(2-chlorophenyl)propyl, 3-(3-chlorophenyl)propyl, 3-(4-chlorophenyl)propyl, 3-(2,4-dichlorophenyl)propyl, 3-(2-fluorophenyl)propyl, 3-(3-fluorophenyl)propyl, 3-(4-fluorophenyl)propyl, 3-(2-methylphenyl)propyl, 3-(3-methylphenyl)propyl, 3-(4-methylphenyl)ethyl, 3-(2-methoxyphenyl)propyl, 3-(3-methoxyphenyl)propyl, 3-(4-methoxyphenyl)propyl, 3-(4-trifluoromethylphenyl)propyl, 3-(2,4-dichlorophenyl)propyl and 3-(3,5-dimethoxyphenyl)
• Typical phenbutyl moieties include are 4-phenylbutyl, 4-(2-chlorophenyl)butyl, 4-(3-chlorophenyl)butyl, 4-(4-chlorophenyl)butyl, 4-(2-fluorophenyl)butyl, 4-(3-fluoro-phenyl)butyl, 4-(4-fluorophenyl)butyl, 4-(2-methylphenyl)butyl, 4-(3-methylphenyl)-butyl, 4-(4-methylphenyl)butyl, 4-(2,4-dichlorophenyl)butyl, 4-(2-methoxphenyl)butyl, 4-(3-methoxyphenyl)butyl and 4-(4-methoxyphenyl)butyl.
• Halogen or halo is defined as iodo, fluoro, bromo and chloro moieties.
• R 2 , R 3 and R 4 , R 5 can exist as cis or trans isomers relative to the heterocyclic ring and R 1 at C-3. These isomers can be separated into individual components by conventional means. Both the individual isomeric compounds and mixtures thereof form subjects of the invention and have fungicidal properties.
• a preferred embodiment of this invention are the compounds, enantiomorphs, salts and complexes of Formula (I') wherein R 2 , R 3 , R 5 are hydrogen, R 1 is aryl or C(R 6 R 7 R 8 ), R is (C 1 -C 12 )alkyl and R 4 is independently aryl, aryloxy(C 1 -C 4 )alkyl, aralkyl, heterocyclic cyano, or (C 1 -C 4 )alkoxycarbonyl.
• a more preferred embodiment of this invention are the compounds, enantiomorphs, salts and complexes of Formula (I'') wherein X is CH, R is methyl and R 1 is C(R 6 R 7 R 8 ) in which R 6 , R 7 , and R 8 are hydrogen.
• Typical compounds encompassed by the present invention of Formula I include those compounds presented in Table 1 of Formula II wherein X is CH, R 2 and R 3 are hydrogen, R 1 is C(R 6 R 7 R 8 ) wherein R 4 , R 5 , R 6 , R 7 , and R 8 are defined in Table 1.
• Typical compounds encompassed by the present invention of Formula I include those compounds presented in Table 2 of Formula III wherein X is nitrogen, R 2 and R 3 are hydrogen, R 1 is C(R 6 R 7 R 8 ) wherein R 6 ,R 7 , and R 8 are defined in Table 2.
• Typical compounds encompassed by the present invention of Formula I include those compounds presented in Table 3 of Formula IV, R 2 , R 3 . and R 5 are hydrogen, and R 1 , R 4 , and X are defined in Table 3.
• Ph is understood to be phenyl
• Scheme A describes the general procedure for the preparation of compounds of the Formula (I). These 3-heterocyclic-3,4,5-substituted isoxazolidines are prepared by the reaction of nitrones (V) with substituted alkenes (VI). The 1,3-dipolar cycloaddition of nitrones to alkenes is described in Advances in Heterocyclic Chemistry , Vol 21., pp.207-251, 1977; Angewandte Chem. Int. Ed. Vol. 2, 565-598, 1963; Synthesis, 205-221, 1975 and in J.Org. Chemistry , Vol. 49, 276-1281, 1984 and references cited therein.
• the cycloaddition can proceed to provide two regioisomers one of which is shown in Scheme A of formula I where R 4 and R 5 are bonded to the carbon adjacent to the oxygen of the isoxazolidine.
• the other regioisomer, where R 2 and R 3 are bonded to the carbon adjacent to the oxygen of the isoxazolidine are also the subject of this invention.
• the regioisomers, when formed can be separated by conventional techniques such as thin layer or column chromatography.
• N-substituted-3,3-disubstituted nitrones of formula V or V' are conducted in solvents such as benzene, toluene and chlorobenzene at temperatures of 50°C to the solvent boiling point and preferably at reflux in toluene.
• the isoxazolidines of the present invention can exist in diastereomeric forms.
• substituents H and R 5 can be cis or trans to the C-3 heterocycle.
• the cis and trans isomers can be separated by standard chromatographic techniques. When separated the isomers are designated isomer A or isomer B with isomer A possessing the higher Rf on thin layer chromatography.
• Scheme B describes the general procedure for the preparation of nitrones V and V'.
• the nitrones of the present invention are N-substituted- ⁇ , ⁇ -disubstituted such that the alpha substituents must be non-hydrogen substituents.
• the chemistry of nitrones, both preparations and reactions, are described in Chem Reviews , Vol. 64, 473-495, 1964.
• the nitrones of the present invention are derived from ketones which bear one heterocycle in the form of 3-pyridyl or 5-pyrimidinyl rings and the other substituent as R 1 defined previously.
• the nitrones are prepared from the corresponding ketone in a hydroxylic solvent such as methanol or ethanol, preferably ethanol, at room temperature to reflux, preferably at room temperature, by the reaction with an R-NHOH for example N-methylhydroxylamine in the form of the hydrochloride salt in the presence of sodium acetate.
• a hydroxylic solvent such as methanol or ethanol, preferably ethanol
• R-NHOH for example N-methylhydroxylamine in the form of the hydrochloride salt in the presence of sodium acetate.
• the nitrone is isolated by removing the solvent followed by trituration of the resulting wet solid with methylene chloride with isolation of the nitrone from the filtrate.
• the nitrones are used directly in the cycloaddition reactions described in scheme A.
• ketones of formula VII and VII' bearing a 3-pyridyl or 5-pyrimidinyl substituents can be prepared by standard synthesis techniques or in the case of 3-acetylpyridine is commercially available.
• March, Advanced Organic Chemistry , 4th Ed, pp. 963-965, and references cited therein, describe the preparation of ketones from nitriles by addition of a Grignard reagent, RMgBr, or an organolithium such as RLi.
• Pyridyl ketones can be prepared by Friedel Crafts acylation as described in Organic Synthesis , Vol. 37, 1957, by magnesium catalyzed acylation to form acetylpyridines as described in Tetrahedron Vol. 48, pp.9233-9236, 1992, and from pyridyl esters by classical Claisen condensation as described in JACS, Vol. 69, 119, 1947 and Vol. 76, 5452, 1954.
• olefins VI and VI'
• ketones VII and VII' To remove the unwanted ketones VII and VII' the mixture is exposed to an alkylhydroxylamine in an alcoholic solvent in the presence of sodium acetate and is stirred at room temperature. The solvent is removed and the residue is dissolved in an organic solvent which is washed thoroughly with water. The water soluble nitrone is removed in the aqueous phase and the resulting organic phase contains the pure desired product.
• the toluene portion was discarded and the acid portion was taken to pH 6 with 10% NaOH.
• This aqueous portion was extracted with several 200ml portions of ethyl acetate. Washed the EtOAc with water and brine, dried over anhydrous sodium sulfate, filtered and stripped to yield an 32 g of an orange oil which was a mixture of the desired product and 3-acetylpyridine.
• the crude reaction mixture was purified by the following process. 32g of the crude mixture as an orange oil was treated with 10g of N -methylhydroxylamine hydrochloride, and 20g of sodium acetate in a 500mL RB flask with 100mL of absolute ethanol. The reaction mixture was stirred overnight at room temperature. The solvent was removed and the residue was dissolved in 150mL of ethyl acetate which was wased with 2 x 100mL water and 1 x 100mL brine.
• 1.23A 1.6(s, 3H), 2.2(d, 6H), 2.6(d, 3H), 2.3-2.9(m, 2H), 5.5(dd, 1H), 6.9-7.5 (m 4H), 7.8 (dd,1H), 8.5(d, 1H) and 8.85(s,1H).
• Numerous compounds of this invention were tested for fungicidal activity in vivo against the diseases described below.
• the compounds were dissolved in a 1:1 mixture of acetone and methanol or N,N-dimethylformamide and diluted with a 2:1:1 mixture of water, acetone and methanol (by volume) to achieve the appropriate concentration.
• the solution was sprayed onto plants and allowed to dry for two hours. Then the plants were inoculated with fungal spores. Each test utilized control plants which were sprayed with the appropriate solvent and inoculated. For these protective tests, the plants were inoculated one day after treating the plants with the compounds of this invention.
• the inoculated plants were placed in a humidity cabinet at 20°C with alternating 12 hours of light and 12 hours of darkness for 7 days.
• the inoculated seedlings were then moved to a controlled environment room at 20°C for 2 days of incubation. Disease control values were recorded as percent control.
• Erysiphe graminis (f. sp. tritici ) was cultured on wheat seedlings, cultivar Fielder, in a controlled temperature room at 18°C. Mildew spores were shaken from the culture plants onto 7-day old wheat seedlings which had been previously sprayed with the fungicide compound. The inoculated seedlings were kept in a controlled temperature room at 18°C and subirrigated. The percent disease control was rated 7 days after the inoculation.
• Sphaerotheca fulginea was maintained on cucumber plants, cultivar Bush Champion, in the greenhouse.
• Inoculum was prepared by placing five to ten heavily mildewed leaves in a glass jar with 500ml of water containing 1 drop of Tween 80 per 100 ml. After shaking the liquid and leaves, the inoculum was filtered through cheese cloth and misted onto the plants with a squirt bottle mister. The spore count was 100,000 spores/ml. The plants were then placed in the greenhouse for infection and incubation. The plants were scored seven days after inoculation. Disease control values were recorded as percent control.
• Cucumber plants were maintained in the greenhouse. Large, fully expanded leaves were collected from the plates. The stems were wrapped with cotton, the leaves were placed in a large petri plate (15-cm. diameter) and the leaves were supported by glass rods. The upper cover of the plate was removed and the upper surface of the detached cucumber leaf was sprayed with the compounds of the present invention. The leaf was allowed to dry in the air for approximately 2 hours.
• the cultures of Botrytis cinerea were maintained on potato dextrose agar for two to three weeks. Agar plugs, 6-mm. in diameter, were cut with a cork borer from the periphery of the fungal colony margin. These agar plugs were placed with the fungal surface in contact with the treated upper surface of the cucumber leaf.
• Cucumber plants were maintained in the greenhouse. Large, fully expanded leaves were collected from the plates. The stems were wrapped with cotton, the leaves were placed in a large petri plate (15-cm. diameter) and the leaves were supported by glass rods. The upper cover of the plate was removed and the upper surface of the detached cucumber leaf was sprayed with the compounds of the present invention. The leaf was allowed to dry in the air for approximately 2 hours. The cultures of Pseudoperonospora cubensis were maintained on cucumber plants. After extracting the spores by shaking the leaves in water, the lower surface of the treated cucumber leaves were sprayed with a spore concentration of 100,000 spores per ml. The plates were returned to a controlled environmental chamber at 20°C and 90% humidity for five days. After this time, leaves were examined for disease development. Data was expressed as percent control.
• the compounds of this invention are useful as agricultural fungicides and, as such, can be applied to various loci such as the seed, the soil or the foliage of plants to be protected.
• the compounds of this invention can be applied as fungicidal sprays by methods commonly employed, such as conventional high-volume hydraulic sprays, low-volume sprays, air-blast spray, aerial sprays and dusts.
• the dilution and rate of application will depend upon the type of equipment employed, the method of application, plants to be treated and diseases to be controlled.
• the compounds of this invention will be applied in amount of from about 0.005 kilogram to about 50 kilograms per hectare and preferably from about 0.025 to about 25 kilograms per hectare of the active ingredient.
• the amount of toxicant coated on the seed is usually at a dosage rate of from about 0.05 to about 20, preferably from about 0.05 to about 4, and more preferably from about 0.1 to about 1 grams per hundred kilograms of seed.
• the chemical can be incorporated in the soil or applied to the surface usually at a rate of from about 0.02 to about 20, preferably from about 0.05 to about 10, and more preferably from about 0.1 to about 5 kilograms per hectare.
• the toxicant is usually applied to growing plants at a rate of from about 0.01 to about 10, preferably from about 0.02 to 5, and more preferably from about 0.25 to about 1 kilograms per hectare.
• fungicidal activity displays fungicidal activity
• these compounds can be combined with other known fungicides to provide broad spectrum activity.
• Suitable fungicides include, but are not limited to, those compounds listed in U.S. Patent Number 5,252,594 (see in particular columns 14 and 15).
• fungicides which an be combined with the compounds of this invention are dimethomorph, cymoxanil, thifluzamide, furalaxyl, ofurace, benalaxyl, oxadixyl, propamocarb, cyprofuram, fenpiclonil, fludioxonil, pyrimethanil, cyprodinil, triticonazole, fluquinconazole, metconazole, spiroxamine, carpropamid, azoxystrobin, kresoxim-methyl, metominostrobin and trifloxystrobin.
• the compounds of this invention can be advantageously employed in various ways. Since these compounds possess broad spectrum fungicidal activity, they can be employed in the storage of cereal grain. These compounds can also be employed as fungicides in cereals including wheat, barley and rye, in rice, peanuts, beans and grapes, on turf, in fruit, nut and vegetable orchards, and for golf course applications.
• diseases against which the compounds of the invention are useful include helminthosporium of corn and barley, wheat and barley powdery mildew, wheat leaf and stem rusts, barley stripe and leaf rust, tomato early blight, tomato late blight, peanut early leaf spot, grape powdery mildew, grape black rot, apple scab, apple powdery mildew, cucumber powdery mildew, brown rot of fruits, botrytis, bean powdery mildew, cucumber anthracnose, wheat septoria nodorum, rice sheath blight and rice blast
• the compounds of the present invention can be used in the form of compositions or formulations.
• Examples of the preparation of compositions and formulations can be found in the American Chemical Society publication “Pesticidal Formulation Research,” (1969), Advances in Chemistry Series No. 86, written by Wade Van Valkenburg; and the Marcel Dekker, Inc. publication “Pesticide Formulations”, (1973) edited by Wade Van Valkenburg.
• the active substance is mixed with conventional inert agronomically acceptable (i.e., plant compatible and/or pesticidally inert) pesticide diluents or extenders such as solid carrier material or liquid carrier material, of the type usable in conventional pesticide compositions or formulations.
• agronomically acceptable carrier any substance which can be used to dissolve, disperse or diffuse the active ingredient in the composition without impairing the active ingredient's effectiveness and which by itself has no significant detrimental effect on the soil, equipment, desirable plants, or agronomic enviornment.
• adjuvants such as surfactants, stabilizers, antifoam agents and anti-drift agents may also be combined.
• compositions and formulations according to the invention are aqueous solutions and dispersions, oily solutions and oil dispersions, pastes, dusting powders, wettable powders, emulsifiable concentrates, flowables, granules, baits, invert emulsions, aerosol compositions and fumigating candles.
• Wettable powders, pastes, flowables and emulsifiable concentrates are concentrated preparations which are diluted with water before or during use. In such formulations, the compounds are extended with a liquid or solid carrier and, when desired, suitable surfactants are incorporated.
• Baits are preparations generally comprising a food or other substance attractive to insects, that includes at least one compound of the instant invention.
• adjuvants such as wetting agents, spreading agents, dispersing agents, stickers, adhesive and the like in accordance with agricultural practices.
• adjuvants such as wetting agents, spreading agents, dispersing agents, stickers, adhesive and the like in accordance with agricultural practices.
• a listing of such adjuvants commonly used in the art, and a discussion of adjuvants, can be found in many references, such as in the John W. McCutcheon, Inc. publication "Detergents and Emulsifiers, Annual.”
• the active compounds of the present invention may be employed alone or in the form of mixtures with one another and/or with such solid and/or liquid dispersible cater vehicles and/or with other known compatible active agents; especially plant protection agents, such as other insecticides, arthropodicides, nematicides, fungicides, bactericides, rodenticides, herbicides, fertilizers, growth-regulating agents, synergists.
• plant protection agents such as other insecticides, arthropodicides, nematicides, fungicides, bactericides, rodenticides, herbicides, fertilizers, growth-regulating agents, synergists.
• the active compound is present in an amount substantially between about 0.0001 (1:999,999) -99 (99:1) % by weight.
• the amount of active ingredient is preferably between about 0.5 (1:199) -90 (9:1) % by weight, and more preferably between about 1(1:99) -75 (3:1) % by weight of the mixture.
• compositions suitable for direct application or field application generally contain the active compound in an amount substantially between about 0.0001 (1:999,999) -95 (19:1) %, preferably between about 0.0005 (1:199,999) -90 (9:1) % by weight, and more preferably between about 0.001 (1:99,999) -75 (3:1) % by weight of the mixture.
• the composition can also be stated as a ratio of the compound to the carrier.
• the weight ratio of these materials (active compound/carrier) can vary from 99:1 (99%) to 1:4 (20%) and more preferably from 10:1 (91%) to 1:3 (25%).
• the compounds of this invention can be dissolved in certain solvents such as acetone, methanol, ethanol, dimethylformamide, pyridine or dimethyl sulfoxide and such solutions can be diluted with water.
• concentrations of the solution can vary from about 1% to about 90% with a preferred range being from about 5% to about 50%.
• the compound can be dissolved in suitable organic solvents, or a mixture of solvents, together with an emulsifying agent to enhance dispersion of the compound in water.
• concentration of the active ingredient in emulsifiable concentrates is usually from about 10% to about 90%, and in flowable emulsion concentrates, can be as high as about 75%.
• Wettable powders suitable for spraying can be prepared by admixing the compound with a finely divided solid, such as clay, inorganic silicate and carbonate, and silica and incorporating wetting agents, sticking agents, and/or dispersing agents in such mixtures.
• concentration of active ingredients in such formulations is usually in the range of from about 20% to about 99%, preferably from about 40% to about 75%.
• a typical wettable powder is made by blending 50 parts of a compound of Formula I, 45 parts of a synthetic precipitated hydrated silicon dioxide, such as that sold under the trademark Hi-SilR, available from PPG Industries, Pittsburgh, PA, and 5 parts of sodium lignosulfonate.
• kaolin type (Barden) clay is used in place of the Hi-Sil in the above wettable powder, and in another such preparation 25% of the Hi-Sil is replaced with a synthetic sodium silicoaluminate sold under the trademark Zeolex®3.
• Dusts are prepared by mixing compounds of Formula I, or the enantiomorphs, salts and complexes thereof with finely divided inert solids which can be organic or inorganic in nature.
• Materials useful for this purpose include botanical flours, silicas, silicates, carbonates and clays.
• One convenient method of preparing a dust is to dilute a wettable powder with a finely divided carrier. Dust concentrates containing from about 20% to about 80% of the active ingredient are commonly made and are subsequently diluted to from about 1% to about 10% use concentration.
• the active compounds can be applied as insecticide sprays by methods commonly employed, such as conventional high-gallonage hydraulic sprays, low gallonage sprays, ultra-low-volume sprays, airblast spray, aerial sprays, and dusts.
• the present invention also contemplates methods of killing, combatting or controlling pests which comprises contacting pests with a combative or toxic amount (i.e. a pesticidally effective amount) of at least one active compound of the invention alone or together with a carrier vehicle (composition or formulation) as noted above.
• a combative or toxic amount i.e. a pesticidally effective amount
• a carrier vehicle composition or formulation
• the term "contacting" as employed in the specification and claims means applying to at least one of (a) such pests and (b) the corresponding habit at thereof (i.e., the locus to be protected, for example, to a growing crop or to an area where a crop is to be grown) the active compound of this invention alone or as a constituent of a composition or formulation.
• the preparations according to the invention may also contain other substances commonly used in preparations of this kind.
• a lubricant such as calcium stearate or magnesium stearate
• a wettable powder or to a mixture to be granulated may be added to a wettable powder or to a mixture to be granulated.
• adheresives such as polyvinylalcohol-cellulose derivatives or other colloidal materials, such as casein, to improve the adherence of the pesticide to the surface to be protected

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